N,N'-Bis(3-nitrobenzylidene)butane-1,4-diamine

ID: ALA2230062

PubChem CID: 76322376

Max Phase: Preclinical

Molecular Formula: C18H18N4O4

Molecular Weight: 354.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(/C=N/CCCC/N=C/c2cccc([N+](=O)[O-])c2)c1

Standard InChI:  InChI=1S/C18H18N4O4/c23-21(24)17-7-3-5-15(11-17)13-19-9-1-2-10-20-14-16-6-4-8-18(12-16)22(25)26/h3-8,11-14H,1-2,9-10H2/b19-13+,20-14+

Standard InChI Key:  FYFMDWSRQXZRIG-IWGRKNQJSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.6978  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1064  -27.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236  -27.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322  -28.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806  -26.8569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1494  -28.2751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5580  -27.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3752  -27.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7838  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6010  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096  -27.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6010  -28.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7838  -28.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096  -26.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6010  -25.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8268  -26.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720  -26.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548  -26.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205  -26.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291  -25.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462  -25.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205  -27.5660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291  -28.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2033  -27.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  4  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  2  0
 14 16  1  0
 10 14  1  0
  6  7  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  2  0
 24 26  1  0
 20 24  1  0
  5 17  2  0
M  CHG  4  14   1  16  -1  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2230062

   1-(3-nitrophenyl)-N-[4-[(3-nitrophenyl)methylideneamino]butyl]methanimine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.37

Molecular Weight (Monoisotopic): 354.1328

AlogP: 3.82

#Rotatable Bonds: 9

Polar Surface Area: 111.00

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.24

CX LogP: 4.13

CX LogD: 4.10

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.29

Np Likeness Score: -0.76

References

1. Aggarwal N, Kumar R, Dureja P, Rawat DS..  (2009)  Schiff bases as potential fungicides and nitrification inhibitors.,  57  (18): [PMID:19702271] [10.1021/jf902035w]

Source

Source(1):

• Scientific Literature